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US4898982A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of diaryl ethers and diaryl sulfides

Assignee: BP Corp North America Inc
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Filing: 1987-11-16
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Granted: 1990-02-06
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Expires: 2007-11-16
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Abstract

Abstract A method is disclosed for the preparation of diaryl ethers and diaryl sulfides by heating a phenol, a thiophenol, a β-hydroxy-substituted fused armomatic ring-system compound or a β-thio-substituted fused aromatic ring-system compound in the presence of thoria deposited on a neutral support.

Inventors

  • 👤 Gregory P. Hussmann

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 05:32
CPC Classifications
C; C07; C07C; C07C321/00; C07C41/00; C07C41/01; C07C41/09

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 81 words
A method for the formation of a diaryl ether or a diaryl sulfide comprising heating a phenol, a thiophenol, a β-hydroxy-substituted fused aromatic ring-system compound, or a β-thio-substituted fused aromatic ring-system compound in the gas phase at a temperature in the range of from about 300° C. to about 600° C. in the presence of a bed of catalyst particles comprising thorium oxide deposited on a support selected from the group consisting of pure silica, pure zirconia, carbon, asbestos and quartz.
Claim 2
Independent Claim 81 words
A method for the formation of a diaryl ether or a diaryl sulfide comprising heating a phenol, a thiophenol, a β-hydroxy-substituted fused aromatic ring-system compound, or a β-thio-substituted fused aromatic ring-system compound in the gas phase at a temperature in the range of from about 300° C. to about 600° C. in the presence of a bed of catalyst particles comprising thorium oxide deposited on a support selected from the group consisting of pure silica, pure zirconia, carbon, asbestos and quartz.
Claim 3
Dependent Claim 21 words
The method of claim 1 comprising heating a phenol or a β-hydroxy-substituted fused aromatic ring-system compound to form a diaryl ether.
Claim 4
Dependent Claim 86 words
The method of claim 2 wherein the phenol or β-hydroxy substituted fused aromatic ring-system compound, apart from the phenolic oxygen substituent therein, either is otherwise unsubstituted or is substituted with either at least one alkyl group containing from 1 to 10 carbon atoms or at least one other substituent that is inert to the coupling reaction, or both, and wherein each aforesaid alkyl and other inert substituent is attached to an aromatic ring carbon atom that is located other than ortho to the phenolic oxygen substituent.
Claim 5
Dependent Claim 22 words
The method of claim 3 wherein the phenol or β-hydroxy-substituted fused aromatic ring-system compound is phenol, m-cresol, p-cresol, 3,4-xylenol, 3,5-xylenol, 3,4,5-trimethylphenol, 5-tetralinol.
Claim 6
Dependent Claim 31 words
The method of claim 2 wherein the phenol or β-hydroxy substituted fused aromatic ring-system compound is dissolved in a solvent that is inert to the formation of the ether or sulfide.
Claim 7
Dependent Claim 20 words
The method of claim 5 wherein the solvent comprises benzene, toluene, a xylene, a hexane, a heptane, tetrahydrofuran, or 1,4-dioxane.
Claim 8
Dependent Claim 32 words
The method of claim 2 wherein a carrier gas that is inert to the coupling reaction is employed to sweep the phenol or β-hydroxy-substituted fused aromatic ring-system compound through the catalyst bed.
Claim 9
Dependent Claim 11 words
The method of claim 7 wherein the carrier gas comprises hydrogen.
Claim 10
Dependent Claim 31 words
The method of claim 1 wherein the catalyst support is pure silica or pure zirconia and contains less then 1000 parts per million of metallic impurities calculated as the elemental metals.
Claim 11
Dependent Claim 14 words
The method of claim 9 wherein the catalyst support is fumed silica or zirconia.
Claim 12
Dependent Claim 34 words
The method of claim 2 wherein the catalyst is formed by calcination at a temperature in the range of from about 600° C. to about 800° C. of thorium salt deposited on the support.
Claim 13
Dependent Claim 22 words
The method of claim 11 wherein the support is calcined at 500° -1000° C. before deposition on it of the thorium salt.
Claim 14
Dependent Claim 22 words
The method of claim 2 wherein the reaction temperature is in the range of from about 425° C. to about 450° C.
Claim 15
Dependent Claim 42 words
The method of claim 13 wherein the reaction temperature is gradually increased at a rate of increase that is from about 0.04° C. to about 0.45° C. per day, within the temperature range of from about 425° C. to about 450° C.

References Cited (Backward Citations)

GB495143A Cited
US2436125A Cited
GB911246A Cited
US4085143A Cited
US4465889A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-02-05 1993-08-07 1994-02-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-02-05 1997-08-07 1998-02-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-02-05 2001-08-07 2002-02-06 $7700.00 Window Closed / Lapsed

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